Organic electroluminescent element, display device and lighting device

ABSTRACT

Disclosed is an organic electroluminescent device having high external quantum efficiency and long life. Also disclosed are an illuminating device and a display device. The organic electroluminescent device is characterized by containing at least one compound having a partial structure represented by the following general formula (1). [chemical formula 1] (1) In the formula, R 1  represents a group (preferably an aromatic hydrocarbon group, an aromatic heterocyclic group, an alkyl group or an alkoxy group) having 4-20 carbon atoms in total and a substituent having a formula weight of 70-350 (preferably an alkyl group or an alkoxy group); R 2 -R 4  independently represent a substituent; n2 represents a number of 0-4; n3 represents a number of 0-2; n4 represents a number of 0-8; and Q represents an atomic group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring.

This is a Continuation of U.S. application Ser. No. 12/442,540 filedMar. 24, 2009, which was a National Phase under 35 USC 371 ofInternational Application PCT/JP2008/050504, filed on Jan. 17, 2008,which claimed the priority of Japanese Application No. 2007/016145,filed Jan. 26, 2007, the entire contents of all three applications arehereby incorporated by reference.

TECHNICAL FIELD

The present invention relates to an organic electroluminescent element,a display device and a lighting device.

BACKGROUND

Conventionally, an emission type electronic display device includes anelectroluminescence display (hereinafter, referred to as an ELD). Aconstituent element of an ELD includes such as an inorganicelectroluminescent element and an organic electroluminescent element. Aninorganic electroluminescent element has been utilized as a flat lightsource, however, it requires a high voltage of alternating current tooperate an emission element. An organic electroluminescent element is anelement provided with a constitution comprising an emitting layercontaining a emitting substance being sandwiched with a cathode and ananode, and an exciton is generated by an electron and a positive holebeing injected into the emitting layer to be recombined, resultingemission utilizing light release (fluorescence•phosphorescence) at thetime of deactivation of said exciton; the emission is possible at avoltage of approximately a few to a few tens volts, and an organicelectroluminescent element is attracting attention with respect to suchas superior viewing angle and high visual recognition due to aself-emission type as well as space saving and portability due to acompletely solid element of a thin layer type.

However, in an organic electroluminescent element in view of the futurepractical application, desired has been development of an organicelectroluminescent element which efficiently emits at a high luminancewith a low electric consumption.

From this reason, many types of organic electroluminescent elements havebeen disclosed (for example, refer to Patent Document 1). In the case ofutilizing emission from an excited singlet as described above, since ageneration ratio of a singlet exciton to a triplet exciton is 1/3, thatis, a generation probability of an emitting exciton species is 25% and alight taking out efficiency is approximately 20%, the limit of anexternal quantum efficiency (ηext) of taking out light is said to be 5%.

However, since an organic electroluminescent element which utilizesphosphorescence from an excited triplet has been reported from PrincetonUniversity (for example, refer to Non-Patent Document 1), researches onmaterials exhibiting phosphorescence at room temperature have come to beactive (for example, refer to Patent Document 2).

Since the upper limit of internal quantum efficiency becomes 100% byutilization of an excited triplet, which is principally 4 times of thecase of an excited singlet, it may be possible to achieve almost thesame ability as a cooled cathode ray tube to attract attention also foran illumination application.

For example, many compounds mainly belonging to heavy metal complexessuch as iridium complexes have been synthesized and studied (forexample, refer to Non-Patent Document 2).

In each case, the luminance of emitted light and the light emissionefficiency are considerably improved compared with usual devices sincethe emitted light is derived from phosphorescence when the lightemission device is prepared by the above materials. There is a problem,however, that the lifetime of light emission is shorter than that of theusual devices. As above-mentioned, it is the present condition that theproperties applicable to practical use cannot be sufficiently attainedyet in the high efficiency phosphorescent light emission material sincethe wavelength of emitted light is difficultly shifted to shorter sideand the light emission lifetime is difficultly improved.

The properties applicable to practical use cannot be sufficientlyattained yet in the high efficiency phosphorescent light emissionmaterial since the wavelength of emitted light is difficultly shifted toshorter side and the light emission lifetime is difficultly improved.

Besides, metal complexes having phenylpyrrazole as the ligand are known,(for example, refer to Patent Documents 3 and 4). Though the lightemission lifetime is improved by the phenylpyrrazole compound having thesubstituting form of the phenyl group to phenylpyrrazole disclosed here,the improvement is not sufficient and there is still room forimprovement from the view point of the light emission efficiency.

On the other hand, it is known that the vacuum vapor deposition methodusually applied to production of organic electroluminescent elementusing a low molecular weight compound causes problems in aspects of theequipment and energy efficiency on the occasion of making large the areaof the organic electroluminescent element. Printing methods including anink-jet method and a screen printing method and coating methodsincluding a spin coat method and a cast coating method are consideredpreferable. Known phosphorescent emission materials suitable forprinting methods or coating methods such as spin coat method and castcoating method are organic metal complexes having a dendrimer portion(for example, refer to Patent Document 5) and organic metal complexeseach fixed in a polymer chain (for example, refer to Patent Document 6).However, there is left room to be improved from the viewpoint of thelifetime and efficiency of the light emission.

-   Patent Document 1: JP-A 3-255190-   Patent Document 2: U.S. Pat. No. 6,097,147-   Patent Document 3: WO 04/085450-   Patent Document 4: JP-A 2005-53912-   Patent Document 5: WO 02/066552-   Patent Document 6: JP-A 2003-342235-   Non-patent Document 1: M. A. Baldo et al., Nature, 395, pp. 151-154,    (1998)-   Non-patent Document 2: S. Lamansky et al., J. Am. Chem. Soc. 123, p.    4304

DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention

An object of the present invention is to provide an organicelectroluminescent element, display device and lighting devicecontaining a novel compound and having high external quantum efficiencyand long lifetime.

Means to Solve the Problems

The above object of the present invention can be attained by thefollowing constitutions.

1. An organic electroluminescent element comprising a compound having apartial structure represented by Formula (1).

In the formula, R¹ is a group substituted by a substituent having 4 to20 carbon atoms and a formula weight of from 70 to 350, R² through R⁴are each independently a substituent, n2 is 0 to 4, n3 is 0 to 4 and n4is 0 to 8. Q is a group of atoms necessary to form an aromatichydrocarbon ring or an aromatic heterocyclic ring.

2. The organic electroluminescent element described in theabove-mentioned item 1, wherein R¹ is a group selected from the groupconsisting of an aromatic hydrocarbon group, an aromatic heterocyclicgroup, an alkyl group and an alkoxyl group.

3. The organic electroluminescent element described in theabove-mentioned items 1 or 2, wherein R¹ has an alkyl group or analkoxyl group each having 4 to 20 carbon atoms.

4. The organic electroluminescent element described in any one of theabove-mentioned items 1 to 3, wherein the partial structure representedby Formula (1) is a partial structure represented by Formula (2).

In the formula, R¹, R² and R³ are each synonymous with R¹, R² and R³ inFormula (1), respectively, R⁵ is a substituent, n2 and n3 are the samenumber as n2 and n3 in Formula (1) and n5 is 0 to 4.

5. The organic electroluminescent element described in theabove-mentioned item 4, wherein R⁵ is a group selected from the groupconsisting of an alkyl group, a cycloalkyl group, an alkenyl group, analkynyl group, an aromatic hydrocarbon ring group, an aromaticheterocyclic group, a heterocyclic group and an alkoxyl group.

6. The organic electroluminescent element described in any one of theabove-mentioned items 1 to 3, wherein the partial structure representedby Formula (1) is a partial structure represented by Formula (3).

In the formula, R¹, R² and R³ are each synonymous with R¹, R² and R³ inFormula (1), respectively, R⁶ is a substituent, n2 and n3 are the samenumber as n2 and n3 in Formula (1), n6 is 0 to 7 and X is a chalcogenatom.

7. The organic electroluminescent element described in theabove-mentioned items 6, wherein R⁵ is a group selected from the groupconsisting of an alkyl group, a cycloalkyl group, an alkenyl group, analkynyl group, an aromatic hydrocarbon ring group, an aromaticheterocyclic group, a heterocyclic group and an alkoxyl group.

8. The organic electroluminescent element comprising an organic layerwhich contains the compound described in any one of the above-mentioneditems 1 to 7.

9. The organic electroluminescent element described in theabove-mentioned item 8, wherein the organic layer is a light emittinglayer.

10. The organic electroluminescent element described in any one of theabove-mentioned items 8 or 9, wherein the organic layer is formed by awet process.

11. A display device having the organic electroluminescent elementdescribed in any one of the above-mentioned items 1 to 10.

12. An lighting device having the organic electroluminescent elementdescribed in any one of the above-mentioned items 1 to 10.

Effects of the Invention

Through the present invention, it was achieved to provide an organicelectroluminescent element, display device and lighting devicecontaining a novel compound and having high external quantum efficiencyand long lifetime.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a schematic drawing to show an example of a display deviceconstituted of an organic electroluminescent element.

FIG. 2 is a schematic drawing of a display section.

FIG. 3 is a schematic drawing of a lighting device.

FIG. 4 is a schematic cross-sectional view of a lighting device.

DESCRIPTION OF SYMBOLS

-   -   1 display    -   3 pixel    -   5 scanning line    -   6 data line    -   7 electrical power line    -   10 organic electroluminescent element    -   11 switching transistor    -   12 operating transistor    -   13 capacitor    -   A display section    -   B control section    -   107 glass substrate having a transparent electrode    -   106 organic EL layer    -   105 cathode    -   102 glass cover    -   108 nitrogen gas    -   109 desiccant

PREFERRED EMBODIMENTS TO CARRY OUT THE INVENTION

The present invention is described in detail bellow.

In the first place, the compounds of the present invention containingthe partial structure represented by Formulas (1), (2) or (3) aredescribed.

<<Compounds Containing the Partial Structure Represented by Formulas(1), (2) or (3)>>

As the aromatic hydrocarbon ring represented by Q in Formula (1), abenzene ring can be cited. The benzene ring may be condensed with anaromatic hydrocarbon ring or the following aromatic heterocyclic ring toform a ring such as a naphthalene ring and a carbazole ring.

As the aromatic heterocyclic ring represented by Q in Formula (1), anoxazole ring, an oxadiazole ring, an oxatriazole ring, an isoxazolering, a tetrazole ring, a thiadiazole ring, a thiatriazole ring, anisothiazole ring, a thiophene ring, a furan ring, a pyrrole ring, animidazole ring, a pyrazole ring, a triazole ring, a pyridine ring, apyridazine ring, a pyrimidine ring, a pyrazine ring, a diazine ring anda triazine ring can be cited.

A benzene ring is particularly preferable as Q in Formula (1).

R¹ in Formula (1) represents a group having a carbon atom number of from4 to 20 in total and a formula weight of from 70 to 350. R¹ ispreferably a group selected from the group consisting of an aromatichydrocarbon ring group, an aromatic heterocyclic group, an alkyl groupand an alkoxyl group.

As the aromatic hydrocarbon ring group (also called as an aromaticcarbon ring group or an aryl group), a phenyl group, a p-chlorophenylgroup, a mesityl group, a tolyl group, a xylyl group, a naphthyl group,an anthoryl group, an azulenyl group, an acenaphthenyl group, afluorenyl group, a phenanthoryl group, an indenyl group, a pyrrenylgroup, a biphenylyl group and a methaterphenyl group can be exemplifiedand the phenyl group is preferable.

As the aromatic heterocyclic group, a furyl group, a thienyl group, apyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinylgroup, a triazinyl group, an imidazolyl group, a pyrazolyl group, athiazolyl group, a quinazolyl group, a carbazolyl group, a carbolinylgroup, a diazacarbazolyl (one formed by replacing one optional carbonatom constituting the carboline ring of the carbolinyl group by anitrogen atom), a phthalazinyl group and a diazacarbazolyl group can beexemplified, and the carbazolyl group is preferable.

As the alkyl group, a methyl group and an ethyl group can be cited andthe methyl group is preferable.

As the alkoxyl group, a methoxy group and an ethoxy group are cited, andthe methoxy group is preferable.

As the alkyl group having a total carbon number of from 4 to 20 and aformula weight of from 70 to 350, a hexyl group, an octyl group, adodecyl group, a tridecyl group, a tetradecyl group and a pentadecylgroup can be cited, which may have a branched or straight structure.Moreover the alkyl group may be an alkyl group having a total number ofcarbon atoms which are bonded through a hetero atom of from 4 to 20 anda formula weight of from 70 to 350 such as a di-trimethylsilyl-methylgroup.

As the alkoxyl group having a total carbon number of from 4 to 20 and aformula weight of from 70 to 350, a hexyloxy group, an octyloxy group,and a dodecyloxy group can be cited, which may have a branched orstraight structure. Moreover the alkoxyl group may be an alkoxyl grouphaving a total number of carbon atoms bonding through a hetero atom offrom 4 to 20 and a formula weight of from 70 to 350 such as a1,3,5-trioxanone group.

In Formula (A), examples of the substituents represented by A1 and A2each include: an alkyl group (for example, a methyl group, an ethylgroup, a propyl group, an isopropyl group, a tert-butyl group, a pentylgroup, a hexyl group, an octyl group, a dodecyl group, a tridecyl group,a tetradecyl group, and a pentadecyl group); a cycloalkyl group (forexample, a cyclopentyl group, and a cyclohexyl group); an alkenyl group(for example, a vinyl group, an allyl group, a 1-propenyl group, a2-butenyl group, a 1,3-butadienyl group, a 2-pentenyl group, and anisopropenyl group); an alkynyl group (for example, an ethynyl group anda propargyl group); an aromatic hydrocarbon ring group (also called anaromatic carbon ring or an aryl group, for example, a phenyl group, ap-chlorophenyl group, a mesityl group, a tolyl group, a xylyl group, anaphthyl group, an anthryl group, an azulenyl group, an acenaphthenylgroup, a fluorenyl group, a phenantolyl group, an indenyl group, apyrenyl group, and a biphenyryl group); an aromatic heterocyclic group(for example, a furyl group, a thienyl group, a pyridyl group, apyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinylgroup, an imidazolyl group, a pyrazolyl group, a thiazolyl group, aquinazolinyl group, a carbazolyl group, a carbolynyl group; adiazacarbazolyl group (which is a group in which one of the carbon atomsconstituting the carboline ring of the above carbolynyl group isreplaced with a nitrogen atom), a phtharadinyl group; a heterocyclicgroup (for example, a pyrrolidyl group, an imidazolidyl group, amorpholyl group, and an oxazilidyl group); an alkoxy group (for example,a methoxy group, an ethoxy group, a propyloxy group, a pentyloxy group,an hexyloxy group, an octyloxy group, and a dodecyloxy group); acycloalkoxy group (for example, a cyclopentyloxy group and acyclohexyloxy group); an aryloxy group (for example, a phenoxy group anda naphthyloxy group); an alkylthio group (for example, a methylthiogroup, an ethylthio group, a propylthio group, a pentylthio group, ahexylthio group, an octylthio group, and a dodecylthio group); acycloalkylthio group (for example, a cyclopentylthio group and acyclohexylthio group); an arylthio group (for example, a phenylthiogroup and a naphthylthio group); an alkoxycarbonyl group (for example, amethyloxycarbonyl group, an ethyloxycarbonyl group, a butyloxycarbonylgroup, an octyloxycarbonyl group, and a dodecyloxycarbonyl group); anaryloxycarbonyl group (for example, a phenyloxycarbonyl group and anaphthyloxycarbonyl group); a sulfamoyl group (for example, anaminosulfonyl group, a methylaminosulfonyl group, adimethylaminosulfonyl group, a butylaminosulfonyl group, ahexylaminosulfonyl group, a cyclohexylaminosulfonyl group, anoctylaminosulfonyl group, a dodecylaminosulfonyl group, aphenylaminosulfonyl group, a naphthylaminosulfonyl group, and a2-pyridylaminosulfonyl group); an acyl group (for example, an acetylgroup, an ethylcarbonyl group, a propylcarbonyl group, a pentylcarbonylgroup, a cyclohexylcarbonyl group, an octylcarbonyl group, a2-ethylhexylcarbonyl group, a dodecylcarbonyl group, a phenylcarbonylgroup, a naphthylcarbonyl group, and a pyridylcarbonyl group); anacyloxy group (for example, an acetyloxy group, an ethylcarbonyloxygroup, a butylcarbonyloxy group, an octylcarbonyloxy group, adodecylcarbonyloxy group, and a phenylcarbonyloxy group); an amido group(for example, a methylcarbonylamino group, an ethylcarbonylamino group,a dimethylcarbonylamino group, a propylcarbonylamino group, apentylcarbonylamino group, a cyclohexylcarbonylamino group, a2-ethylhexylcarbonylamino group, an octylcarbonylamino group, adodecylcarbonylamino group, a phenylcarbonylamino group, and anaphthylcarbonylamino group); a carbamoyl group (for example, anaminocarbonyl group, a methylaminocarbonyl group, adimethylaminocarbonyl group, a propylaminocarbonyl group, apentylaminocarbonyl group, a cyclohexylaminocarbonyl group, anoctylaminocarbonyl group, a 2-ethylhexylaminocarbonyl group, adodecylaminocarbonyl gropup, a phenylaminocarbonyl group, anaphthylaminocarbonyl group, and a 2-pyridylaminocarbonyl group); aureido group (for example, a methylureido group, an ethylureido group, apentylureido group, a cyclohexylureido group, an octylureido group, adodecylureido group, a phenylureido group, a naphthylureido group, and a2-oyridylaminoureido group); a sulfinyl group (for example, amethylsulfinyl group, an ethylsulfinyl group, a butylsulfinyl group, acyclohexylsulfinyl group, a 2-ethylhexylsulfinyl group, adodecylsulfinyl group, a phenylsulfinyl group, a naphthylsulfinyl group,and a 2-pyridylsulfinyl group); an alkylsulfonyl group (for example, amethylsulfonyl group, an ethylsulfonyl group, a butylsulfinyl group, acyclohexylsulfonyl group, a 2-ethylhexylsulfonyl group, and adodecylsulfonyl group, an arylsulfonyl group or a heteroarylsulfonylgroup (for example, a phenylsulfonyl group, a naphthylsulfonyl group,and a 2-pyridylsulfonyl group); an amino group (for example, an aminogroup, an ethylamino group, a dimethylamino group, a butylamino group, acyclopentylamino group, a dodecylamino group, an anilino group, anaphthylamino group, and a 2-pyridylamino group); a cyano group; a nitrogroup; a hydroxyl group; a mercapto group; a silyl group (for example, atrimethylsilyl group, a triisopropylsilyl group, a triphenylsilyl group,and a phenyldiethylsilyl group), and a phosphono group.

These substituents may be further substituted by the above substituents.A plurality of the substituents may form a ring by bonding with eachother.

In Formula (1), n2 is 0 to 4 and preferably 0 or 1, n3 is 0 to 2 andpreferably 0 and n4 is 0 to 8 and preferably 0 or 1.

In Formula (2), R¹, R² and R³ are each synonymous with the grouprepresented by R¹, R² and R³ in Formula (1), respectively, and n2 and n3each represent the same number as that represented by n2 and n3 inFormula (1).

R⁵ represents a substituent which is synonymous with the group describedas to R¹, R² and R³ in Formula (1), and n5 is 0 to 4 and preferably 0 or1.

In Formula (3), R¹, R² and R³ each represents the groups synonymous withthose represented by R¹, R² and R³ in Formula (1) and n2 and n3 eachrepresents the same number as that represented by n2 and n3 in Formula(1).

R⁶ represents a substituent synonymous with the group described as toR¹, R² and R³ in Formula (1), and n6 is 0 to 7 and preferably 0 or 1.

The compound of the present invention having the partial structurerepresented by Formulas (1), (2) or (3) is expanded in planar andspatial direction. As a result of that, effects of that the film formingability is improved and the concentration quenching is inhibited by thespatial expansion so that the host-free can be attained.

Concrete examples of the compound containing the partial structurerepresented by any one of Formulas (1), (2) and (3) are shown below.However, the present invention is not limited to them.

The compounds having a partial structure represented by one of Formulas(1) to (3) of the present invention can be synthesized by applying amethod described in such as Organic Letter, vol. 3, No. 16, pp.2579-2581 (2001), Inorganic Chemistry vol. 30, No. 8, pp. 1685-1687(1991), J. Am. Chem. Soc., vol. 123, p. 4304 (2001), Inorganic Chemistryvol. 40, No. 7, pp. 1704-1711 (2001), Inorganic Chemistry vol. 41, No.12, pp. 3055-3066 (2002), New Journal of Chemistry, vol. 26, p. 1171(2002), Angewandte Chemie International Edition, vol. 38, pp. 1698-1712(1999), Bulletin of the Chemical Society of Japan, vol. 71, pp. 467-473(1998), J. Am. Chem. Soc., vol. 125, No. 18, p. 5274-5275 (2003), and J.Am. Chem. Soc., vol. 125, No. 35, p. 10580-10585 (2003), and referencedocuments described in these documents.

Typical synthesis example of a compound of the present invention isdescribed below for reference.

(Synthesis of Compound 1-19)

Synthesis of a Ligand (Compound <19b>)

Into a three-necked 200 ml flask, 5.0 g of Compound <19a> (a compounddescribed in Org. Lett., 2006 (13), 2779-2782) and 0.2 g of[1,3-bis(diphenylphosphino)propane]nickel(II) chloride were charged andthe atmosphere in the flask was replaced by nitrogen. And then 100 ml oftetrahydrofuran was added and 11 ml of a 2 moles/L tetrahydrofuransolution of hexylmagnesium chloride was dropped spending 30 minutes.After finishing of the dropping, the system was heated and refluxed for6 hours and then cooled to a room temperature and the reacting liquidwas slowly poured into 500 ml of ice water. The organic layer wasseparated, washed by a saturated sodium chloride solution and dried bymagnesium sulfate. The resultant was concentrated under reduced pressurein a rotary evaporator and the obtained residue was purified by columnchromatography. It was confirmed by ¹H-NMR and Mass-spectrogram that theobtained substance was the objective compound.

Synthesis of Compound 1-19

Into a 100 ml three-necked flask, 0.2 g of Compound <19b> and 0.8 g ofiridium(III) chloride trihydrate were charged and the atmosphere in thesystem was replaced by nitrogen and then 50 ml of 2-ethanolamine and 10ml of purified water added. The system was heated and stirred at 130° C.for 4 hours, and then 50 ml of methanol was added. Resultantprecipitates were separated by filtration and dried to obtain 2.1 g ofCompound <19c>.

Into a 100 ml flask, 1.0 g of Compound <19c>, 0.73 g of Compound <19b>and 0.33 g of silver trifluoroacetate were charged and the atmosphere inthe flask was replaced by nitrogen. After that, 30 ml of 2-ethoxyethanolwas added and the system was heated and stirred at 110° C. for 24 hours.After finishing of reaction, 60 ml of methanol was added. Resultantprecipitates were separated by filtration and purified by columnchromatography and sublimation to obtain 130 mg of solid substance. Itwas confirmed by ¹H-NMR and Mass-spectrogram that the obtained substancewas the objective compound.

Specific examples of a preferable layer constitution of an organicelectroluminescent element of the present invention are shown below;however, the present invention is not limited thereto.

(i) anode/light emitting layer/electron transport layer/cathode(ii) anode/positive hole transport layer/light emitting layer/electrontransport layer/cathode(iii) anode/positive hole transport layer/light emitting layer/positivehole inhibition layer/electron transport layer/cathode(iv) anode/positive hole transport layer/light emitting layer/positivehole inhibition layer/electron transport layer/cathode bufferlayer/cathode(v) anode/anode buffer layer/positive hole transport layer/lightemitting layer/positive hole inhibition layer/electron transportlayer/cathode buffer layer/cathode

In the organic EL element of the present invention, the maximumwavelength of light emitted from the blue light emitting layer ispreferably within 430-480 nm, and the green light emitting layer ispreferably a monochromatic light emitting layer which results in themaximum wavelength of the emitted light within 510-550 nm, while the redlight emitting layer is a monochromatic light emitting layer whichresults in the maximum wavelength of the emitted light in the range of600-640 nm. Display devices employing these are preferred. Further, awhile light emitting layer is acceptable, which is prepared bylaminating at least three of these layers. Further, between the lightemitting layers may be present a non-light emitting intermediate layer.As the organic EL element of the present invention, preferred is a whitelight emitting layer, and illuminating devices employing these arepreferred.

Each of the layers which constitute the organic electroluminescentelements of the present invention will now be sequentially detailed.

<<Emitting Layer>>

The emitting layer of the present invention is a layer, which emitslight via recombination of electrons and positive holes injected from anelectrode or a layer such as an electron transport layer or a positivehole transport layer. The emission portion may be present either withinthe emitting layer or at the interface between the emitting layer and anadjacent layer thereof.

The total thickness of the light emitting layer is not particularlylimited. However, in view of the layer homogeneity, the minimization ofapplication of unnecessary high voltage during light emission, and thestability enhancement of the emitted light color against the driveelectric current, the layer thickness is regulated preferably in therange of 2 nm-5 μm, more preferably in the range of 2 nm-200 nm, butmost preferably in the range of 10-20 nm.

With regard to preparation of the light emitting layer, light emittingdopants and host compounds, described below, may be subjected to filmformation via a conventional thin filming method such as a vacuumdeposition method, a spin coating method, a casting method, an LBmethod, or an ink-jet method.

It is preferable that the light emitting layer of the organic EL elementof the present invention incorporates host compounds and at least onekind of light emitting dopants (also referred to as phosphorescencedopants or phosphorescence emitting dopants) and fluorescence dopants.

(Host Compounds (Also Referred to as Light Emitting Hosts)

Host compounds employed in the present invention will now be described.

“Host compounds”, as described in the present invention, are defined ascompounds, incorporated in a light emitting layer, which result in aweight ratio of at least 20% in the above layer and also result in aphosphorescent quantum yield of the phosphorescence emission of lessthan 0.1. Further, of compounds incorporated in the light emittinglayer, it is preferable that the weight ratio in the aforesaid layer isat least 20%.

An emission host compound of the present invention may be used withplural known host compounds. It is possible to control the transfer ofcharges by making use of a plurality of host compounds, which results inhigh efficiency of an organic electroluminescent element. In addition,it is possible to mix a different emission lights by making use of aplurality of emission dopants that will be described later. Any requiredemission color can be obtained thereby.

Further, an emission host of the present invention may be either a lowmolecular weight compound or a polymer compound having a repeating unit,in addition to a low molecular weight compound provided with apolymerizing group such as a vinyl group and an epoxy group (anevaporation polymerizing emission host).

A known emission host which may be jointly used is preferably a compoundhaving a positive hole transporting ability and an electron transportingability, as well as preventing elongation of an emission wavelength andhaving a high Tg (a glass transition temperature).

As specific examples of an emission host compounds described in thefollowing Documents are preferable.

For example, JP-A Nos. 2001-257076, 2002-308855, 2001-313179,2002-319491, 2001-357977, 2002-334786, 2002-8860, 2002-334787,2002-15871, 2002-334788, 2002-43056, 2002-334789, 2002-75645,2002-338579, 2002-105445, 2002-343568, 2002-141173, 2002-352957,2002-203683, 2002-363227, 2002-231453, 2003-3165, 2002-234888,2003-27048, 2002-255934, 2002-260861, 2002-280183, 2002-299060,2002-302516, 2002-305083, 2002-305084 and 2002-308837.

The following compounds can also be cited.

(Emission Dopant)

The emission dopant of the present invention will now be described.

As light emitting dopants according to the present invention, employedmay be fluorescent dopants (also referred to as fluorescent compounds),phosphorescence emitting dopants (also referred to as phosphorescentdopants, phosphorescent compounds, phosphorescence emitting compounds,or phosphorescent dopants). However, in view of production of organic ELelements exhibiting higher light emission efficiency, as light emittingdopants (also referred simply to as light emitting materials) employedin the light emitting layer of the organic EL element and light emittingunits in the present invention, it is preferable to simultaneouslyincorporate the aforesaid host compounds and the phosphorescenceemitting dopants.

(Phosphorescence-Emitting Dopant)

A phosphorescence emitting dopant of the present invention will bedescribed.

The phosphorescence-emitting dopant of the present invention is acompound, wherein emission from an excited triplet state thereof isobserved, specifically, emitting phosphorescence at room temperature(25° C.) and exhibiting a phosphorescence quantum yield of at least 0.01at 25° C. The phosphorescence quantum yield is preferably at least 0.1.

The phosphorescence quantum yield can be determined via a methoddescribed in page 398 of Bunko II of Dai 4 Han Jikken Kagaku Koza 7(Spectroscopy II of 4th Edition Lecture of Experimental Chemistry 7)(1992, published by Maruzen Co., Ltd.). The phosphorescence quantumyield in a solution can be determined using appropriate solvents.However, it is only necessary for the phosphorescence-emitting dopant ofthe present invention to exhibit the above phosphorescence quantum yieldusing any of the appropriate solvents.

Two kinds of principles regarding emission of a phosphorescence-emittingdopant are cited. One is an energy transfer-type, wherein carriersrecombine on a host compound on which the carriers are transferred toproduce an excited state of the host compound, and then via transfer ofthis energy to a phosphorescence-emitting dopant, emission from thephosphorescence-emitting dopant is realized. The other is a carriertrap-type, wherein a phosphorescence-emitting dopant serves as a carriertrap and then carriers recombine on the phosphorescence-emitting dopantto generate emission from the phosphorescence-emitting dopant. In eachcase, the excited state energy of the phosphorescence-emitting dopant isrequired to be lower than that of the host compound.

Ones selected from known substances usually used in the light emittinglayer of organic electroluminescent element can be used for thephosphorescent dopant.

The phosphorescent dopant relating to the present invention ispreferably a complex compound containing a metal of Groups 8 to 10 ofperiodic table and more preferably an iridium compound, an osmiumcompound, a platinum compound (platinum complex type compound) and arare metal complex. Among them, the iridium compounds are preferred andthe compounds having the partial structure of the present inventionrepresented by Formulas (1), (2) or (3) are most preferable.

It is preferable in the present invention that the following concretecompound is used together with the compound having the partial structureof the present invention represented by Formulas (1), (2) or (3).

Concrete examples of known compound usable as the phosphorescent dopantare shown below but the present invention is not limited to thesecompounds. These compounds can be synthesized by the method described inInorg. Chem., 40, 1704-1711.

(Fluorescent Dopants (Also Referred to as Fluorescent Compounds))

As fluorescent dopants, listed are coumarin based dyes, pyran baseddyes, cyanine based dyes, croconium based dyes, squarylium based dyes,oxobenzanthracene based dyes, fluorescein based dyes, Rhodamine baseddyes, pyrylium based dyes, perylene based dyes, stilbene based dyes,polythiophene based dyes, or rare earth complex based fluorescentmaterials.

An injection layer, an inhibition layer, and an electron transportlayer, which are employed as a constituting layer of the organic ELelement of the present invention will now be described.

<Injection Layer: Electron Injection Layer, Positive Hole InjectionLayer>

An injection layer is appropriately provided and an injection layerincludes an electron injection layer and a positive hole injectionlayer, which may be arranged between an anode and an emitting layer or apositive transfer layer, and between a cathode and an emitting layer oran electron transfer layer, as described above.

An injection layer is a layer which is arranged between an electrode andan organic layer to decrease an operating voltage and to improve anemission luminance, which is detailed in volume 2, chapter 2 (pp.123-166) of “Organic EL Elements and Industrialization Front thereof(Nov. 30, 1998, published by N. T. S Corp.)”, and includes a positivehole injection layer (an anode buffer layer) and an electron injectionlayer (a cathode buffer layer).

An anode buffer layer (a positive hole injection layer) is also detailedin such as JP-A 9-45479, 9-260062 and 8-288069, and specific examplesinclude such as a phthalocyanine buffer layer comprising such as copperphthalocyanine, an oxide buffer layer comprising such as vanadium oxide,an amorphous carbon buffer layer, and a polymer buffer layer employingconductive polymer such as polythiophene.

A cathode buffer layer (an electron injection layer) is also detailed insuch as JP-A 6-325871, 9-17574 and 10-74586, and specific examplesinclude a metal buffer layer comprising such as strontium and aluminum,an alkali metal compound buffer layer comprising such as lithiumfluoride, an alkali earth metal compound buffer layer comprising such asmagnesium fluoride, and an oxide buffer layer comprising such asaluminum oxide. The above-described buffer layer (injection layer) ispreferably a very thin layer, and the layer thickness is preferably in arange of 0.1-100 nm although it depends on a raw material.

<Inhibition Layer: Positive Hole Inhibition Layer, Electron InhibitionLayer>

An inhibition layer is appropriately provided in addition to the basicconstitution layers composed of organic thin layers as described above.Examples are described in such as JP-A Nos. 11-204258 and 11-204359 andp. 273 of “Organic Electroluminescent Elements and IndustrializationFront Thereof (Nov. 30 (1998), published by N. T. S Corp.)” isapplicable to a positive hole inhibition (hole block) layer according tothe present invention.

A positive hole inhibition layer, in a broad meaning, is provided with afunction of electron transport layer, being composed of a materialhaving a function of transporting an electron but a very small abilityof transporting a positive hole, and can improve the recombinationprobability of an electron and a positive hole. by inhibiting a positivehole while transporting an electron. Further, a constitution of anelectron transport layer described later can be appropriately utilizedas a positive hole inhibition layer according to the present invention.

The positive hole inhibition layer of the organic EL element of thepresent invention is preferably arranged adjacent to the light emittinglayer.

It is preferable that the positive hole inhibition layer incorporatescarbazole derivatives listed as a host compound described above.

Further, in the present intention, in the case in which a plurality oflight emitting layers which differ in a plurality of different emittedlight colors, it is preferable that the light emitting layer whichresults in the shortest wavelength of the emitted light maximumwavelength is nearest to the anode in all light emitting layers.However, in such a case, it is preferable to additionally arrange thepositive hole inhibition layer between the aforesaid shortest wavelengthlayer and the light emitting layer secondly near the anode. Further, atleast 50% by weight of the compounds incorporated in the positive holeinhibition layer arranged in the aforesaid position preferably exhibitsthe ionization potential which is greater by at least 0.3 eV than thatof the host compounds of the aforesaid shortest wavelength lightemitting layer.

The ionization potential is defined as energy which is necessary torelease electrons in the HOMO (being the highest occupied molecularorbital) to the vacuum level, and may be determined via, for example,the method described below.

(1) By employing Gaussian98 (Gauaaian98, Revision A. 11. 4, M. J.Frisch, et al. Gaussian 98(Gaussian98, Revision A. 11. 4, M. J. Frisch,et al, Gaussian, Inc., Pittsburgh Pa., 2002), which is a molecularorbital calculation software, produced by Gaussian Co. in the UnitedState of America, and by employing B3LYP/6-31G* as a key word, the value(in terms of corresponding eV unit) was computed, and it is possible toobtain the ionization potential by rouging off the second decimal point.The background, in which the resulting calculated values are effective,is that the calculated values obtained by the above method exhibit highrelationship with the experimental values.(2) It is possible to determine the ionization potential via a method inwhich ionization potential is directly determined employing aphotoelectron spectrometry. For example, by employing a low energyelectron spectrophotometer “Model AC-1”, produced by Riken Keiki Co., orappropriately employ a method known as an ultraviolet light electronspectrometry.

On the other hand, the electron inhibition layer, as described herein,has a function of the positive hole transport layer in a broad sense,and is composed of materials having markedly small capability ofelectron transport, while having capability of transporting positiveholes and enables to enhance the recombination probability of electronsand positive holes by inhibiting electrons, while transportingelectrons. Further, it is possible to employ the constitution of thepositive hole transport layer, described below, as an electroninhibition layer when needed. The thickness of the positive holeinhibition layer and the electron transport layer according to thepresent invention is preferably 3-100 nm, but is more preferably 5-30nm.

<Positive Hole Transport Layer>

A positive hole transport layer contains a material having a function oftransporting a positive hole, and in a broad meaning, a positive holeinjection layer and an electron inhibition layer are also included in apositive hole transport layer. A single layer of or plural layers of apositive hole transport layer may be provided.

A positive hole transport material is those having any one of a propertyto inject or transport a positive hole or a barrier property to anelectron, and may be either an organic substance or an inorganicsubstance. For example, listed are a triazole derivative, an oxadiazolederivative, an imidazole derivative, a polyarylalkane derivative, apyrazolone derivative, a phenylenediamine derivative, an arylaminederivative, an amino substituted chalcone derivative, an oxazolederivatives, a styrylanthracene derivative, a fluorenone derivative, ahydrazone derivative, a stilbene derivative, a silazane derivative, ananiline type copolymer, or conductive polymer oligomer and specificallypreferably such as thiophene oligomer.

As a positive hole transport material, those described above can beutilized, however, it is preferable to utilized a porphyrin compound, anaromatic tertiary amine compound and a styrylamine compound, andspecifically preferably an aromatic tertiary amine compound.

Typical examples of an aromatic tertiary amine compound and astyrylamine compound include N,N,N′,N′-tetraphenyl-4,4′-diaminophenyl;N,N′-diphenyl-N,N′-bis(3-methylphenyl)-(1,1′-biphenyl)-4,4′-diamine(TDP); 2,2-bis(4-di-p-tolylaminophenyl)propane;1,1-bis(4-di-p-tolylaminophenyl)cyclohexane; N,N,N′,N′-tetra-p-tolyl4,4′-diaminobiphenyl;1,1-bis(4-di-p-tolylaminophenyl)-4-phenylcyclohexane;bis(4-dimethylamino-2-methyl)phenylmethane;bis(4-di-p-tolylaminophenyl)phenylmethane;N,N′-diphenyl-N,N′-di(4-methoxyphenyl)-4,4′-diaminobiphenyl;N,N,N′,N′-tetraphenyl-4,4′-diaminophenylether;4,4′-bis(diphenylamino)quadriphenyl; N,N,N-tri(p-tolyl)amine;4-(di-p-tolylamino)-4′-[4-(di-p-triamino)styryl]stilbene;4-N,N-diphenylamino-(2-diphenylvinyl)benzene;3-methoxy-4′-N,N-diphenylaminostilbene; and N-phenylcarbazole, inaddition to those having two condensed aromatic rings in a moleculedescribed in U.S. Pat. No. 5,061,569, such as4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NDP), and4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MDTDATA),in which three of triphenylamine units are bonded in a star burst form,described in JP-A 4-308688.

Polymer materials, in which these materials are introduced in a polymerchain or constitute the main chain of polymer, can be also utilized.Further, an inorganic compound such as a p type-Si and a p type-SiC canbe utilized as a positive hole injection material and a positive holetransport material

Further, it is possible to employ so-called p type positive holetransport materials, as described in Japanese Patent Publication Open toPublic Inspection (hereinafter referred to as JP-A) No. 11-251067, andJ. Huang et al. reference (Applied Physics Letters 80 (2002), p. 139).In the present invention, since high efficiency light emitting elementsare prepared, it is preferable to employ these materials.

The positive hole transport layer can be prepared by forming a thinlayer made of the above-described positive hole transport materialaccording to a method well known in the art such as a vacuum evaporationmethod, a spin coating method, a cast method, an inkjet method and a LBmethod. The layer thickness of a positive hole transport layer is notspecifically limited, however, it is generally 5 nm-5 μm, and preferably5 nm-200 nm. This positive transport layer may have a single layerstructure composed of one or not less than two types of the abovedescribed materials.

Further, it is possible to employ a positive hole transport layer of ahigher p property which is doped with impurities. As its example, listedare those described in each of JP-A Nos. 4-297076, 2000-196140,2001-102175, as well as in J. Appl. Phys., 95, 5773 (2004).

In the present invention, it is preferable to employ a positive holetransport layer of such a high p property, since it is possible toproduce an element of lower electric power consumption.

<Electron Transport Layer>

An electron transfer layer is composed of a material having a functionto transfer an electron, and an electron injection layer and a positivehole inhibition layer are included in an electron transfer layer in abroad meaning. A single layer or plural layers of an electron transferlayer may be provided.

Heretofore, when an electron transport layer is composed of single layerand a plurality of layers, electron transport materials (alsofunctioning as a positive hole inhibition material) employed in theelectron transport layer adjacent to the cathode side with respect tothe light emitting layer, electrons ejected from the cathode may betransported to the light emitting layer. As such materials, any of theconventional compounds may be selected and employed. Examples of thesecompounds include such as a nitro-substituted fluorene derivative, adiphenylquinone derivative, a thiopyradineoxide derivative,carbodiimide, a fluorenylidenemethane derivative,anthraquinonedimethane, an anthraquinone derivative, an anthronederivative and an oxadiazole derivative. Further, a thiazole derivativein which an oxygen atom in the oxadiazole ring of the above-describedoxadiazole derivative is substituted by a sulfur atom, and a quinoxalinederivative having a quinoxaline ring which is known as an electronattracting group can be utilized as an electron transfer material.Polymer materials, in which these materials are introduced in a polymerchain or these materials form the main chain of polymer, can be alsoutilized.

Further, a metal complex of a 8-quinolinol derivative such astris(8-quinolinol)aluminum (Alq),tris(5,7-dichloro-8-quinolinol)aluminum,tris(5,7-dibromo-8-quinolinol)aluminum,tris(2-methyl-8-quinolinol)aluminum, tris(5-methyl-8-quinolinol)aluminumand bis(8-quinolinol) zinc (Znq); and metal complexes in which a centralmetal of the aforesaid metal complexes is substituted by In, Mg, Cu, Ca,Sn, Ga or Pb, can be also utilized as an electron transfer material.

Further, metal-free or metal phthalocyanine, or those the terminal ofwhich is substituted by an alkyl group and a sulfonic acid group, can bepreferably utilized as an electron transfer material. Further,distyrylpyrazine derivative, which has been exemplified as a material ofan emitting layer, can be also utilized as an electron transfermaterial, and, similarly to the case of a positive hole injection layerand a positive hole transfer layer, an inorganic semiconductor such asan n-type-Si and an n-type-SiC can be also utilized as an electrontransfer material.

This electron transport layer can be prepared by forming a thin layermade of the above-described electron transport material according to amethod well known in the art such as a vacuum evaporation method, a spincoating method, a cast method, an inkjet method and a LB method. Thelayer thickness of an electron transport layer is not specificallylimited; however, it is generally 5 nm-5 μm, and preferably 5 nm-200 nm.This electron transport layer may have a single layer structure composedof one or not less than two types of the above described materials.

Further, it is possible to employ an electron transport layer doped withimpurities, which exhibits high n property. Examples thereof includethose, described in JP-A Nos. 4-297076, 10-270172, 2000-196140,2001-102175, as well as J. Appl. Phys., 95, 5773 (2004).

The present invention is preferable since by employing an electrontransport layer of such a high n property electron transport layer, itis possible to preparer an element of further lowered electric powerconsumption.

<Anode>

As an anode according to an organic electroluminescent element of thepresent invention, those comprising metal, alloy, a conductive compound,which is provided with a large work function (not less than 4 eV), and amixture thereof as an electrode substance are preferably utilized.Specific examples of such an electrode substance include a conductivetransparent material such as metal like Au, CuI, indium tin oxide (ITO),SnO₂ and ZnO. Further, a material such as IDIXO (In₂O₃—ZnO), which canprepare an amorphous and transparent electrode, may be also utilized. Asfor an anode, these electrode substances may be made into a thin layerby a method such as evaporation or spattering and a pattern of a desiredform may be formed by means of photolithography, or in the case ofrequirement of pattern precision is not so severe (not less than 100μm), a pattern may be formed through a mask of a desired form at thetime of evaporation or spattering of the above-described substance.

Alternatively, when coatable materials such as organic electricallyconductive compounds are employed, it is possible to employ a wet systemfilming method such as a printing system or a coating system. Whenemission is taken out of this anode, the transmittance is preferably setto not less than 10% and the sheet resistance as an anode is preferablynot more than a few hundreds Ω/□. Further, although the layer thicknessdepends on a material, it is generally selected in a range of 10-1,000nm and preferably of 10-200 nm.

<Cathode>

On the other hand, as a cathode according to the present invention,metal, alloy, a conductive compound and a mixture thereof, which have asmall work function (not more than 4 eV), are utilized as an electrodesubstance. Specific examples of such an electrode substance includessuch as sodium, sodium-potassium alloy, magnesium, lithium, amagnesium/copper mixture, a magnesium/silver mixture, amagnesium/aluminum mixture, a magnesium/indium mixture, analuminum/aluminum oxide (Al₂O₃) mixture, indium, a lithium/aluminummixture and rare earth metal.

Among them, with respect to an electron injection property anddurability against such as oxidation, preferable are a mixture ofelectron injecting metal with the second metal which is stable metalhaving a work function larger than electron injecting metal, such as amagnesium/silver mixture, a magnesium/aluminum mixture, amagnesium/indium mixture, an aluminum/aluminum oxide (Al₂O₃) mixture anda lithium/aluminum mixture, and aluminum. As for a cathode, theseelectrode substances may be made into a thin layer by a method such asevaporation or spattering.

Further, the sheet resistance as a cathode is preferably not more than afew hundreds Ω/□ and the layer thickness is generally selected in arange of 10-1,000 nm and preferably of 10-200 nm.

Herein, to transmit emission, either one of an anode or a cathode of anorganic electroluminescent element is preferably transparent ortranslucent to improve the mission luminance.

Further, after forming, on the cathode, the above metals at a filmthickness of 1-20 nm, it is possible to prepare a transparent ortranslucent cathode in such a manner that electrically conductivetransparent materials are prepared thereon. By applying the above, it ispossible to produce an element in which both anode and cathode aretransparent.

<Substrate>

A substrate according to an organic electroluminescent element of thepresent invention is not specifically limited to a specific type ofsubstrate such as glass and plastics. They may be transparent or opaque.

However, a transparent substrate is preferable when the emitting lightis taken from the side of substrate. Substrates preferably utilizedincludes such as glass, quartz and transparent resin film. Aspecifically preferable substrate is resin film capable of providing anorganic electroluminescent element with a flexible property.

Resin film includes such as: polyesters such as polyethyleneterephthalate (PET) and polyethylene naphthalate (PEN); polyethylene,polypropyrene; cellulose esters or their derivatives such as cellophane,cellulose diacetate, cellulose triacetate, cellulose acetate butylate,cellulose acetate propionate (CAP), cellulose acetate phthalate (TAC)and cellulose nitrate; polyvinylidene chloride, polyvinyl alcohol,polyethylene vinyl alcohol, syndiotactic polystyrene, polycarbonate,norbornene resin, polymethylpentene, polyether ketone, polyimide,polyether sulfone (PES), polyphenylene sulfide, polysulfones,polyetherimide, polyether ketone imide, polyamide, fluororesin, Nylon,polymethylmethacrylate, acrylic resin, polyacrylate; and cycloolefineresins such as ARTON (produced by JSR Co. Ltd.) and APEL (produce byMitsui Chemicals, Inc.)

On the surface of a resin film, formed may be a film incorporatinginorganic and organic compounds or a hybrid film of both. Barrier filmsare preferred at a water vapor permeability (25±0.5° C., and relativehumidity (90±2) % RH) of at most 0.01 g/(m²·24 h), determined based onJIS K 7129-1992. Further, high barrier films are preferred at an oxygenpermeability of at most 1×10⁻³ ml/(m²·24 h·MPa), and at a water vaporpermeability of at most 10⁻⁵ g/(m²·24 h), determined based on JIS K7126-1987.

As materials forming a barrier film, employed may be those which retardpenetration of moisture and oxygen, which deteriorate the element. Forexample, it is possible to employ silicon oxide, silicon dioxide, andsilicon nitride. Further, in order to improve the brittleness of theaforesaid film, it is more preferable to achieve a laminated layerstructure of inorganic layers and organic layers. The laminating orderof the inorganic layer and the organic layer is not particularlylimited, but it is preferable that both are alternatively laminated aplurality of times.

Barrier film forming methods are not particularly limited, and examplesof employable methods include a vacuum deposition method, a sputteringmethod, a reactive sputtering method, a molecular beam epitaxy method, acluster ion beam method, an ion plating method, a plasma polymerizationmethod, a plasma CVD method, a laser CVD method, a thermal CVD method,and a coating method. Of these, specifically preferred is a methodemploying an atmospheric pressure plasma polymerization method,described in JP-A No. 2004-68143.

Examples of opaque support substrates include metal plates such aluminumor stainless steel, films, opaque resin substrates, and ceramicsubstrates.

The external extraction efficiency of light emitted by the organic ELelement of the present invention is preferably at least 1% at roomtemperature, but is more preferably at least 5%. External extractionquantum yield (%)=the number of photons emitted by the organic ELelement to the exterior/the number of electrons fed to organic ELelement

Further, even by simultaneously employing color hue improving filterssuch as a color filter, simultaneously employed may be color conversionfilters which convert emitted light color from the organic EL element tomulticolor by employing fluorescent materials. When the color conversionfilters are employed, it is preferable that λmax of light emitted by theorganic EL element is at least 480 nm.

<<Sealing>>

As sealing means employed in the present invention, listed may be, forexample, a method in which sealing members, electrodes, and a supportingsubstrate are subjected to adhesion via adhesives.

The sealing members may be arranged to cover the display region of anorganic EL element, and may be an engraved plate or a flat plate.Neither transparency nor electrical insulation is limited.

Specifically listed are glass plates, polymer plate-films, metal plates,and films. Specifically, it is possible to list, as glass plates,soda-lime glass, barium-strontium containing glass, lead glass,aluminosilicate glass, borosilicate glass, bariumborosilicate glass, andquartz. Further, listed as polymer plates may be polycarbonate, acryl,polyethylene terephthalate, polyether sulfide, and polysulfone. As ametal plate, listed are those composed of at least one metal selectedfrom the group consisting of stainless steel, iron, copper, aluminummagnesium, nickel, zinc, chromium, titanium, molybdenum, silicon,germanium, and tantalum, or alloys thereof.

In the present invention, since it is possible to convert the element toa thin film, it is possible to preferably employ a metal film. Further,the oxygen permeability of the polymer film is preferably at most 1×10⁻³ml/(m²·24 h·MPa), determined by the method based on JIS K 7126-1987,while its water vapor permeability (at 25±0.5° C. and relative humidity(90±2) %) is at most 10⁻⁵ g/(m²·24 h), determined by the method based onJIS K 7129-1992.

Conversion of the sealing member into concave is carried out employing asand blast process or a chemical etching process.

In practice, as adhesives, listed may be photo-curing and heat-curingtypes having a reactive vinyl group of acrylic acid based oligomers andmethacrylic acid, as well as moisture curing types such as2-cyanoacrylates. Further listed may be thermal and chemical curingtypes (mixtures of two liquids) such as epoxy based ones. Still furtherlisted may be hot-melt type polyamides, polyesters, and polyolefins. Yetfurther listed may be cationically curable type ultraviolet radiationcurable type epoxy resin adhesives.

In addition, since an organic EL element is occasionally deterioratedvia a thermal process, those are preferred which enable adhesion andcuring between room temperature and 80° C. Further, desiccating agentsmay be dispersed into the aforesaid adhesives. Adhesives may be appliedonto sealing portions via a commercial dispenser or printed on the samein the same manner as screen printing.

Further, it is appropriate that on the outside of the aforesaidelectrode which interposes the organic layer and faces the supportsubstrate, the aforesaid electrode and organic layer are covered, and inthe form of contact with the support substrate, inorganic and organicmaterial layers are formed as a sealing film. In this case, as materialsforming the aforesaid film may be those which exhibit functions toretard penetration of those such as moisture or oxygen which results indeterioration. For example, it is possible to employ silicon oxide,silicon dioxide, and silicon nitride. Still further, in order to improvebrittleness of the aforesaid film, it is preferable that a laminatedlayer structure is formed, which is composed of these inorganic layersand layers composed of organic materials. Methods to form these filmsare not particularly limited. It is possible to employ, for example, avacuum deposition method, a sputtering method, a reactive sputteringmethod, a molecular beam epitaxy method, a cluster ion beam method, anion plating method, a plasma polymerization method, an atmosphericpressure plasma polymerization method, a plasma CVD method, a thermalCVD method, and a coating method.

In a gas phase and a liquid phase, it is preferable to inject inertgases such as nitrogen or argon, and inactive liquids such asfluorinated hydrocarbon or silicone oil into the space between thesealing member and the surface region of the organic EL element.Further, it is possible to form vacuum. Still further, it is possible toenclose hygroscopic compounds in the interior.

Examples of hygroscopic compounds include metal oxides (for example,sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesiumoxide, and aluminum oxide); sulfates (for example, sodium sulfate,calcium sulfate, magnesium sulfate, and cobalt sulfate); metal halides(for example, calcium chloride, magnesium chloride, cesium fluoride,tantalum fluoride, cerium bromide, magnesium bromide, barium iodide, andmagnesium iodide); perchlorates (for example, barium perchlorate andmagnesium perchlorate). In sulfates, metal halides, and perchlorates,suitably employed are anhydrides.

<<Protective Film and Protective Plate>>

The aforesaid sealing film on the side which nips the organic layer andfaces the support substrate or on the outside of the aforesaid sealingfilm, a protective or a protective plate may be arranged to enhance themechanical strength of the element. Specifically, when sealing isachieved via the aforesaid sealing film, the resulting mechanicalstrength is not always high enough, whereby it is preferable to arrangethe protective film or the protective plate described above. Usablematerials for these include glass plates, polymer plate-films, and metalplate-films which are similar to those employed for the aforesaidsealing. However, in terms of light weight and a decrease in thickness,it is preferable to employ polymer films.

<<Light Extraction>>

It is generally known that an organic EL element emits light in theinterior of the layer exhibiting the refractive index (being about1.7-about 2.1) which is greater than that of air, whereby only about15-about 20% of light generated in the light emitting layer isextracted. This is due to the fact that light incident to an interface(being an interface of a transparent substrate to air) at an angle of θwhich is at least critical angle is not extracted to the exterior of theelement due to the resulting total reflection, or light is totallyreflected between the transparent electrode or the light emitting layerand the transparent substrate, and light is guided via the transparentelectrode or the light emitting layer, whereby light escapes in thedirection of the element side surface.

Means to enhance the efficiency of the aforesaid light extractioninclude, for example, a method in which roughness is formed on thesurface of a transparent substrate, whereby total reflection isminimized at the interface of the transparent substrate to air (U.S.Pat. No. 4,774,435), a method in which efficiency is enhanced in such amanner that a substrate results in light collection (JP-A No.63-314795), a method in which a reflection surface is formed on the sideof the element (JP-A No. 1-220394), a method in which a flat layer of amiddle refractive index is introduced between the substrate and thelight emitting body and an antireflection film is formed (JP-A No.62-172691), a method in which a flat layer of a refractive index whichis equal to or less than the substrate is introduced between thesubstrate and the light emitting body (JP-A No. 2001-202827), and amethod in which a diffraction grating is formed between the substrateand any of the layers such as the transparent electrode layer or thelight emitting layer (including between the substrate and the outside)(JP-A No. 11-283751).

In the present invention, it is possible to employ these methods whilecombined with the organic EL element of the present invention. Of these,it is possible to appropriately employ the method in which a flat layerof a refractive index which is equal to or less than the substrate isintroduced between the substrate and the light emitting body and themethod in which a diffraction grating is formed between the substrateand any of the layers such as the transparent electrode layer or thelight emitting layer (including between the substrate and the outside).

By combining these means, the present invention enables the productionof elements which exhibit higher luminance or excel in durability.

When a low refractive index medium of a thickness, which is greater thanthe wavelength of light, is formed between the transparent electrode andthe transparent substrate, the extraction efficiency of light emittedfrom the transparent electrode to the exterior increases as therefractive index of the medium decreases.

As materials of the low refractive index layer, listed are, for example,aerogel, porous silica, magnesium fluoride, and fluorine based polymers.Since the refractive index of the transparent substrate is commonlyabout 1.5-about 1.7, the refractive index of the low refractive indexlayer is preferably at most approximately 1.5, but is more preferably atmost 1.35.

Further, thickness of the low refractive index medium is preferably atleast two times the wavelength in the medium. The reason is that whenthe thickness of the low refractive index medium reaches nearly thewavelength of light so that electromagnetic waves oozed via evernescententer into the substrate, effects of the low refractive index layer arelowered.

The method in which the interface which results in total reflection or adiffraction grating is introduced in any of the media is characterizedin that light extraction efficiency is significantly enhanced. The abovemethod works as follows. By utilizing properties of the diffractiongrating capable of changing the light direction to the specificdirection different from diffraction via so-called Bragg diffractionsuch as primary diffraction or secondary diffraction of the diffractiongrating, of light emitted from the light emitting layer, light, which isnot emitted to the exterior due to total reflection between layers, isdiffracted via introduction of a diffraction grating between any layersor in a medium (in the transparent substrate and the transparentelectrode) so that light is extracted to the exterior.

It is preferable that the introduced diffraction grating exhibits atwo-dimensional periodic refractive index. The reason is as follows.Since light emitted in the light emitting layer is randomly generated toall directions, in a common one-dimensional diffraction gratingexhibiting a periodic refractive index distribution only in a certaindirection, light which travels to the specific direction is onlydiffracted, whereby light extraction efficiency is not sufficientlyenhanced. However, by changing the refractive index distribution to atwo-dimensional one, light, which travels to all directions, isdiffracted, whereby the light extraction efficiency is enhanced.

As noted above, a position to introduce a diffraction grating may bebetween any layers or in a medium (in a transparent substrate or atransparent electrode). However, a position near the organic lightemitting layer, where light is generated, is desirous.

In this case, the cycle of the diffraction grating is preferably about½-about 3 times the wavelength of light in the medium.

The preferable arrangement of the diffraction grating is such that thearrangement is two-dimensionally repeated in the form of a squarelattice, a triangular lattice, or a honeycomb lattice.

<<Light Collection Sheet>>

Via a process to arrange a structure such as a micro-lens array shape onthe light extraction side of the organic EL element of the presentinvention or via combination with a so-called light collection sheet,light is collected in the specific direction such as the front directionwith respect to the light emitting element surface, whereby it ispossible to enhance luminance in the specific direction.

In an example of the micro-lens array, square pyramids to realize a sidelength of 30 μm and an apex angle of 90 degrees are two-dimensionallyarranged on the light extraction side of the substrate. The side lengthis preferably 10-100 μm. When it is less than the lower limit,coloration results due to generation of diffraction effects, while whenit exceeds the upper limit, the thickness increases undesirably.

It is possible to employ, as a light collection sheet, for example, onewhich is put into practical use in the LED backlight of liquid crystaldisplay devices. It is possible to employ, as such a sheet, for example,the luminance enhancing film (BEF), produced by Sumitomo 3M Limited. Asshapes of a prism sheet employed may be, for example, Δ shaped stripesof an apex angle of 90 degrees and a pitch of 50 μm formed on a basematerial, a shape in which the apex angle is rounded, a shape in whichthe pitch is randomly changed, and other shapes.

Further, in order to control the light radiation angle from the lightemitting element, simultaneously employed may be a light diffusionplate-film. For example, it is possible to employ the diffusion film(LIGHT-UP), produced by Kimoto Co., Ltd.

<<Preparation Method of Organic EL Element>>

As one example of the preparation method of the organic EL element ofthe present invention, the preparation method of the organic EL elementcomposed of anode/positive hole injection layer/positive hole transportlayer/light emitting layer/electron transport layer/electron injectionlayer/cathode will be described.

Initially, a thin film composed of desired electrode substances, forexample, anode substances is formed on an appropriate base material toreach a thickness of at most 1 μm but preferably 10-200 nm, employing amethod such as vapor deposition or sputtering, whereby an anode isprepared.

Subsequently, on the above, formed are organic compound thin layersincluding a positive hole injection layer, a positive hole transportlayer, a light emitting layer, a positive hole inhibition layer, anelectron transport layer, and an electron injection layer, which areorganic EL element materials.

Methods to form each of these layers include, as described above, avapor deposition method and a wet process (a spin coating method, acasting method, an ink-jet method, and a printing method). In thepresent invention, in view of easy formation of a homogeneous film andrare formation of pin holes, preferred is film formation via the coatingmethod such as the spin coating method, the ink-jet method, or theprinting method.

As liquid media which are employed to dissolve or disperse organic metalcomplexes according to the present invention, employed may be, forexample, ketones such as methyl ethyl ketone or cyclohexanone; fattyacid esters such as ethyl acetate; halogenated hydrocarbons such asdichlorobenzene; aromatic hydrocarbons such as toluene, xylene,mesitylene and cyclohexylbenzene; aliphatic hydrocarbons such ascyclohexane, decaline and dodecane; and organic solvents such as DMF orDMSO. Further, with regard to dispersion methods, it is possible toachieve dispersion employing dispersion methods such as ultrasonicwaves, high shearing force dispersion or media dispersion.

After forming these layers, a thin layer composed of cathode materialsis formed on the above layers via a method such as vapor deposition orsputtering so that the film thickness reaches at most 1 μm, but ispreferably in the range of 50-200 nm, whereby a cathode is arranged, andthe desired organic EL element is prepared.

Further, by reversing the preparation order, it is possible to achievepreparation in order of a cathode, an electron injection layer, anelectron transport layer, a light emitting layer, a positive holetransport layer, a positive hole injection layer, and an anode. Whendirect current voltage is applied to the multicolor display deviceprepared as above, the anode is employed as +polarity, while the cathodeis employed as −polarity. When 2-40 V is applied, it is possible toobserve light emission. Further, alternating current voltage may beapplied. The wave form of applied alternating current voltage is notspecified.

<<Application>>

It is possible to employ the organic EL element of the present inventionas display devices, displays, and various types of light emittingsources. Examples of light emitting sources include, but are not limitedto lighting apparatuses (home lighting and car lighting), clocks,backlights for liquid crystals, sign advertisements, signals, lightsources of light memory media, light sources of electrophotographiccopiers, light sources of light communication processors, and lightsources of light sensors.

If needed, the organic EL element of the present invention may undergopatterning via a metal mask or an ink-jet printing method during filmformation. When the patterning is carried out, only an electrode mayundergo patterning, an electrode and a light emitting layer may undergopatterning, or all element layers may undergo patterning. Duringpreparation of the element, it is possible to employ conventionalmethods.

Color of light emitted by the organic EL element of the presentinvention and compounds according to the present invention is specifiedas follows. In FIG. 4.16 on page 108 of “Shinpen Shikisai KagakuHandbook (New Edition Color Science Handbook)” (edited by The ColorScience Association of Japan, Tokyo Daigaku Shuppan Kai, 1985), valuesdetermined via a spectroradiometric luminance meter CS-1000 (produced byKonica Minolta Sensing Inc.) are applied to the CIE chromaticitycoordinate, whereby the color is specified.

Further, when the organic EL element of the present invention is a whiteelement, “white”, as described herein, means that when 2-degree viewingangle front luminance is determined via the aforesaid method,chromaticity in the CIE 1931 Color Specification System is within theregion of X=0.33±0.07 and Y=0.33±0.07.

EXAMPLES

The present invention is described below referring examples but thepresent invention is not limited to them.

Example 1 Preparation of Organic Electroluminescent Element 1

A glass substrate of 100 mm×100 mm×1.1 mm on which an ITO (indium tinoxide) layer of 100 nm was provided as an anode (NA-45 manufactured byNH Techno Glass Corp.) was subjected to patterning and thus obtainedtransparent substrate plate having the ITO transparent anode was washedby ultrasonic treatment using isopropyl alcohol, dried by dried nitrogengas and subjected to UV-ozone cleaning for 5 minutes.

On the transparent substrate plate, a solution prepared by dilutingpoly(3,4-ethylenedioxythiophene)-polystyrene-sulfonate (PEDOT/PSS,Baytron P Al 4083 manufactured by Bayer) with purified water by 70weight percent was coated by spin coating at 3,000 rpm for 30 secondsand dried under vacuum for 1 hour at 200° C. to provide a first positivehole transfer layer.

On the first positive hole transfer layer, a solution prepared bydissolving 30 mg of m-CP and 1.5 mg of Compound A-1 in 3 ml of toluenewas coated by spin coating at 1,000 rpm for 30 seconds and dried undervacuum for 1 hour at 60° C. to form a light emitting layer having athickness of 80 nm.

Thus obtained substrate was attached in a vacuum vapor depositionapparatus and the pressure in the vacuum chamber was reduced by 4×10⁻⁴Pa and 10 nm of calcium as a buffer layer and 110 nm of aluminum as acathode were deposited to prepare Organic Electroluminescent Element1-1.

<<Preparation of Organic Electroluminescent Elements 1-2 Through 1-5>>

Organic Electroluminescent Elements 1-2 Through 1-5 were prepared in thesame manner as in Organic Electroluminescent Element 1-1 except thatCompound A-1 used for formation of the light emitting layer was replacedby the compound having the partial structure represented by Formulas(1), (2) or (3) of the present invention as shown in the column of metalcomplex compound of Table 1.

<<Organic Electroluminescent Elements 1-1 Through 1-5>>

On the occasion of evaluation of Organic Electroluminescent Elements 1-1through 1-5, the non-light emitting side of each of the organicelectroluminescent elements was covered with a glass case and a sealingglass plate having a thickness of 300 μm on which an epoxy type photocurable adhesive, Laxtruck LC0629B manufactured by Toagosei Co., Ltd.,was applied was piled on the cathode and contacted with the transparentsubstrate plate, and then irradiated with UV rays to cure the adhesiveto prepare a lighting device to be evaluated shown in FIGS. 3 and 4.

FIG. 3 shows a schematic drawing of the lighting device, in which theorganic electroluminescent element 101 was covered by the glass cover102. The sealing operation using the glass cover was carried out innitrogen atmosphere (high purity nitrogen gas of not less than 99.999)in a glove box for preventing contact of the organic electroluminescentelement 101 with air. FIG. 4 shows a cross section of the lightingdevice, in which 105 is the cathode, 106 is the electroluminescent layerand 107 is the glass substrate plate with the transparent electrode.Interior of the glass cover is filled by nitrogen gas 108 and moisturecapturing agent 109 is provided.

<<External Quantum Efficiency>>

As to each of the prepared organic electroluminescent elements, theexternal quantum efficiency was determined when a constant electriccurrent of 2.5 mA/cm² was applied at 23° C. in a dried nitrogenatmosphere. A spectral emission luminance meter CS-1000, manufactured byKonica Minolta Sensing Corp., was used for the determination.

<<Light Emission Lifetime>>

The time necessary for reducing by half the luminance of the emittedlight just after the starting of light emission when the device wasdriven by a constant electric current of 2.5 mA/cm² at 23° C. in a driednitrogen atmosphere was measured and the time was referred to as ahalf-lifetime (τ^(1/2)) and used as an indicator of the life time. Thespectral emission luminance meter CS-1000, manufactured by KonicaMinolta Sensing Corp., was also used for the determination.

The measured results of the external quantum efficiency and the lightemission lifetime of Organic Electroluminescent Elements 1-1 through 1-5were relatively evaluated when the values of Organic ElectroluminescentElements 1-5 were each set at 100.

The obtained results are listed in Table 1.

TABLE 1 Metal External Organic complex quantum Element compoundefficiency Lifetime Remarks 1-1 A-1  100 100 Comparative 1-2 1-1  112130 Inventive 1-3 1-13 121 142 Inventive 1-4 1-47 118 122 Inventive 1-51-52 109 186 Inventive

It is clear from Table 1 that the raising of the efficiency and lifetimeare attained by the organic electroluminescent elements using thecompound of the present invention containing the partial structurerepresented by Formulas (1), (2) or (3) compared with the organicelectroluminescent element using the comparative compound.

Example 2 Preparation of Organic Electroluminescent Element 2-1

A glass substrate of 100 mm×100 mm×1.1 mm on which an ITO (indium tinoxide) layer of 100 nm was provided as an anode (NA45 manufactured by NHTechno Glass Corp.) was subjected to patterning and thus obtainedtransparent substrate plate having the ITO transparent anode was washedby ultrasonic treatment using isopropyl alcohol, dried by dried nitrogengas and subjected to UV-ozone cleaning for 5 minutes.

The substrate was attached onto a spin coater and coated with a solutionprepared by dilutingpoly(3,4-ethylenedioxy-thiophene)-polystyrene-sulfonate (PEDOT/PSS,Baytron P Al 4083 manufactured by Bayer) with purified water by 70weight percent by spin coating at 3,000 rpm for 30 seconds and driedunder vacuum for 1 hour at 200° C. to provide a positive hole injectionlayer with a thickness of 30 nm.

After the drying treatment, the substrate was attached again onto thespin coater and coated with a solution prepared by dissolving 60 mg ofCompound A-2 in 6 ml of cyclohexane by spin coating at 1,000 rpm for 30seconds (layer thickness of 40 nm) and dried for 1 hour at 60° C. undervacuum and then irradiated with UV rays for 5 minutes to form a positivehole transfer layer.

The substrate was attached onto the spin coater in the same manner as inthe formation of the positive hole transfer layer and coated with asolution prepared by dissolving 60 mg of CPB and 3 mg of Compound 1-19of the present invention in 6 ml of cyclohexane at 1,000 rpm for 30seconds (layer thickness of 40 nm) and dried for 1 hour at 60° C. toform a light emitting layer.

The resultant substrate was fixed on a substrate holder of a vacuumvapor deposition apparatus and a molybdenum resistance heating boatcontaining 200 mg of Bathocuproine (BCP) and another molybdenumresistance heating boat containing 200 mg of Alq₃ were set in the vacuumvapor deposition apparatus.

After reducing the pressure in the vacuum chamber until 4×10⁻⁴ Pa, theheating boat containing BCP was heated by applying electric current fordepositing BCP on the light emitting layer at a deposition rate of 0.1nm/sec to provide a positive hole blocking layer with a layer thicknessof 10 nm.

Moreover, the heating boat containing Alq₃ was heated by applyingelectric current for depositing Alq₃ on the positive hole blocking layerat a deposition rate of 0.1 nm/sec to provide an electron transfer layerwith a layer thickness of 40 nm. The temperature of the substrate on theoccasion of the vapor deposition was room temperature.

After that, 0.5 nm of lithium fluoride and 110 nm of aluminum were vapordeposited to form a cathode. Thus Organic Electroluminescent Element 2-1was prepared. Green light was emitted when electric current was appliedto thus obtained device and it was confirmed that the device could beused as an organic electroluminescent display device.

Furthermore, organic electroluminescent elements were each prepared byreplacing Compound 1-19 of the present invention used in OrganicElectroluminescent Element 2-1 by Compound 1-2, 1-7, 1-11, 1-20, 1-33,1-41, 1-55 and 1-56, respectively, which contain one of the partialstructure represented by Formulas (1), (2) or (3), and the similarresults were obtained.

Example 3 Preparation of Full-Color Display Apparatus

(Blue Light Emission Organic Electroluminescent Element)

Organic Electroluminescent 1-2 prepared in Example 1 was used as a bluelight emission Organic Electroluminescent Element 3-1 (Blue).

(Green Light Emission Organic Electroluminescent Element)

Green light emission Organic Electroluminescent Element 3-2 (Green) wasprepared in the same manner as in Organic Electroluminescent Element 1-2except that Compound 1-1 of the present invention was replaced byCompound 1-21 of the present invention.

(Red Light Emission Organic Electroluminescent Element)

Red light emission Organic Electroluminescent Element 3-3 (Red) wasprepared in the same manner as in Organic Electroluminescent Element 1-2except that Compound 1-1 of the present invention was replaced byCompound 1-55 of the present invention.

An active matrix type full-color display apparatus having theconstitution shown in FIG. 1 was prepared by arranging the red, greenand blue light emission organic electroluminescent elements on a plane.In FIG. 2, the schematic drawing of displaying part A of theabove-prepared displaying apparatus is only displayed. The apparatus hasa wiring part including plural scanning lines 5, scanning lines 6 andthe arranged plural pixels 3 (pixels each emitting light in red range,green range or blue range) on the same substrate, the scanning lines andthe plural data lines are each made from an electro-conductive materialand crossed at right angles in a lattice state and connected with thepixel at the crossing point (details are not displayed in the drawing).The plural pixels are driven by an active matrix system having theorganic electroluminescent elements corresponding to each of the colors,a switching transistor as the active element and a driving transistor.The light emission device receives image data signals from the data line6 and emits light corresponding to the received signals when scanningsignals are applied from the scanning line 5. A full-color displayingapparatus was prepared by suitably arranging the red, green and bluepixels as above-mentioned.

It was continued by driving the above-prepared full-color displayingapparatus that a full-color displaying apparatus having high lightemission efficiency and long light emission lifetime could be obtained.

Example 4 Preparation of White Lighting Device

White light emission Organic Electroluminescent Element 4-1 (White) wasprepared in the same manner as in Organic Electroluminescent Element 1-2except that Compound 1-1 of the present invention was replaced by amixture of Compound 1-1 and Compound 1-51 of the present invention.

When thus obtained Organic Electroluminescent Element 4-1 was evaluated,the non light emission side of device was covered by a glass case in thesame manner as in Example 1 to prepare an lighting device. The lightingdevice could be used as a thin-type lighting device having high lightemission efficiency and low light emission lifetime.

Example 5

Organic Electroluminescent Element 5-1 was prepared in the same manneras in Organic Electroluminescent Element 1-1 except that Compound m-CPused in the light emitting layer was replaced by Compound 2-2. Moreover,Organic Electroluminescent Elements 5-2 through 5-5 were prepared in thesame manner as in Organic Electroluminescent Element 5-1 except thatCompound 1 used for forming the light emitting layer was replaced by acompound having one of the partial structures represented by Formulas(1), (2) or (3) which are shown in the column of metal complex compoundof Table 2.

Thus obtained Organic Electroluminescent Elements 5-1 through 5-5 wereevaluated in the same manner as in Example 1. The evaluation results areshown in Table 2.

TABLE 2 Metal External Organic complex quantum element compoundefficiency Lifetime Remarks 5-1 A-1  100 100 Comparative 5-2 1-1  133180 Inventive 5-3 1-13 124 165 Inventive 5-4 1-66 141 142 Inventive 5-51-67 122 121 Inventive

It is clear from Table 2 that the raising of the efficiency and lifetimeare attained by the organic electroluminescent elements using thecompound of the present invention containing the partial structurerepresented by Formulas (1), (2) or (3) compared with the organicelectroluminescent element using the comparative compound.

What we claim is:
 1. An organic electroluminescent element comprising acompound having a partial structure represented by Formula (1) in themolecule:

wherein R¹ is an aromatic hydrocarbon group or an aromatic heterocyclicgroup substituted by a substituent having 4 to 20 carbon atoms and aformula weight of 70 to 350, and substituent is selected from the groupconsisting of: an alkyl group, an alkoxyl group, a cycloalkyl group, anaryl group and an aromatic heterocyclic group; R² through R⁴ are eachindependently a substituent; n2 is an integer of 0 to 4; n3 is aninteger of 0 to 4; n4 is an integer of 0 to 8; and Q is a group of atomsnecessary to form an aromatic hydrocarbon ring or an aromaticheterocyclic ring.
 2. The organic electroluminescent element of claim 1,wherein R¹ is an aromatic hydrocarbon group substituted by a substituenthaving 4 to 20 carbon atoms and a formula weight of 70 to 350, andsubstituent is selected from the group consisting of: an alkyl group, analkoxyl group, a cycloalkyl group, an aryl group and an aromaticheterocyclic group.
 3. The organic electroluminescent element of claim1, wherein R¹ is a phenyl group substituted by a substituent having 4 to20 carbon atoms and a formula weight of 70 to 350, and substituent isselected from the group consisting of: an alkyl group, an alkoxyl group,a cycloalkyl group, an aryl group and an aromatic heterocyclic group. 4.The organic electroluminescent element of claim 1, wherein the partialstructure represented by Formula (1) is further represented by Formula(2):

wherein R¹, R² and R³ are each synonymous with R¹, R² and R³ in Formula(1), respectively; R⁵ is a substituent; n2 and n3 are the same number asn2 and n3 in Formula (1); and n5 is an integer of 0 to
 4. 5. The organicelectroluminescent element of claim 4, wherein R⁵ is a group selectedfrom the group consisting of an alkyl group, a cycloalkyl group, analkenyl group, an alkynyl group, an aromatic hydrocarbon ring group, anaromatic heterocyclic group, a heterocyclic group and an alkoxyl group.6. The organic electroluminescent element of claim 1, wherein thepartial structure represented by Formula (1) is further represented byFormula (3):

wherein R¹, R² and R³ are each synonymous with R¹, R² and R³ in Formula(1), respectively; R⁶ is a substituent; n2 and n3 are the same number asn2 and n3 in Formula (1); n6 is an integer of 0 to 7; and X is achalcogen atom.
 7. The organic electroluminescent element of claim 6,wherein R⁶ is a group selected from the group consisting of an alkylgroup, a cycloalkyl group, an alkenyl group, an alkynyl group, anaromatic hydrocarbon ring group, an aromatic heterocyclic group, aheterocyclic group and an alkoxyl group.
 8. The organicelectroluminescent element comprising an organic layer which containsthe compound described in claim
 1. 9. The organic electroluminescentelement of claim 8, wherein the organic layer is a light emission layer.10. The organic electroluminescent element of claim 8, wherein theorganic layer is formed by a wet process.
 11. A display device havingthe organic electroluminescent element of claim
 1. 12. A lighting devicecomprising the organic electroluminescent element of claim 1.